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62176220(PyBOX)<sub>2</sub>-Yb(OTf)<sub>3</sub> catalysed asymmetric acyl-PS formation of KAB26-21
Experiments
plus.google.com-+KatrinaBadiolaKatrina Badiola [b][u]Hazard and Risk Assessment[/b][/u] [data]4712[/data] [b][u]Previous Experiments[/b][/u] [blog]6069[/blog] [blog]6168[/blog] [b][u]Chemical Information[/u][/b] [b]2-(3,4-dimethoxyphenyl)-N-(4-nitrobenzylidene)ethanamine (MNR42-1)[/b] - SMILES: O=[N+]([O-])C1=CC=C(/C=N/CCC2=CC(OC)=C(OC)C=C2)C=C1, InChI: InChI=1S/C17H18N2O4/c1-22-16-8-5-13(11-17(16)23-2)9-10-18-12-14-3-6-15(7-4-14)19(20)21/h3-8,11-12H,9-10H2,1-2H3/b18-12-, InChIKey: LMBMXYXQVBPKHJ-PDGQHHTCSA-N. [b]1-(6,7-dimethoxy-1-(4-nitrophenyl)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone (KAB26-18) -[/b] SMILES: O=[N+]([O-])C1=CC=C(C2N(C(C)=O)CCC3=CC(OC)=C(OC)C=C32)C=C1, InChI: InChI=1S/C19H20N2O5/c1-12(22)20-9-8-14-10-17(25-2)18(26-3)11-16(14)19(20)13-4-6-15(7-5-13)21(23)24/h4-7,10-11,19H,8-9H2,1-3H3, InChIKey: OIFIJKJQAGAGKY-UHFFFAOYSA-N. [b][u]Procedure[/b][/u] [i]NOTE: All THF was dried over microwave activated 3 Å molecular sieves (2.0-2.5 mm) >72 h prior to use. All acetonitrile was dried over microwave 3 Å molecular sieves (2.0-2.5 mm) >24 h prior to use.[1] All glassware used was dried overnight at 115 °C.[/i] [b][u]Summary and Conclusion[/b][/u] [b][u]References[/b][/u] [1] D. Bradley, G. Williams and M. Lawton, [i]J. Org. Chem.[/i] [b]2010[/b], [i]75[/i], 8351. DOI: 10.1021/jo101589h [url=http://dx.doi.org/10.1021/jo101589h]Paper[/url]. [2] H. Ishitani and S. Kobayashi, [i]TetLett[/i] [b]1996[/b], [i]37[/i], 7357. [3] S. Watanabe, Y. Kobayashi, T. Arai, H. Sasai, M. Bougauchi and M. Shibaski, [i]TetLett[/i] [b]1998[/b], [i]39[/i], 7353. [4] Rare-Earth Metal Triflates in Organic Synthesis, S. Kobayashi, M. Sugiura, H. Kitagawa and W. W.-L. Lam, [i]Chem. Rev.[/i] [b]2002[/b], [i]102[/i], 2227–2302. DOI: 10.1021/cr010289i [url=http://dx.doi.org/10.1021/cr010289i]Paper[/url]. ------------------------------------------ NOTES ------------------------------------------]]>FINISH: 27/07/12




Hazard and Risk Assessment
HRA KAB26-18


Previous Experiments
Preparation of MNR42-1
Yb(OTf)3/PyBOX catalysed asymmetric acyl-PS formation of KAB26-17

Chemical Information
2-(3,4-dimethoxyphenyl)-N-(4-nitrobenzylidene)ethanamine (MNR42-1) - SMILES: O=[N+]([O-])C1=CC=C(/C=N/CCC2=CC(OC)=C(OC)C=C2)C=C1, InChI: InChI=1S/C17H18N2O4/c1-22-16-8-5-13(11-17(16)23-2)9-10-18-12-14-3-6-15(7-4-14)19(20)21/h3-8,11-12H,9-10H2,1-2H3/b18-12-, InChIKey: LMBMXYXQVBPKHJ-PDGQHHTCSA-N.
1-(6,7-dimethoxy-1-(4-nitrophenyl)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone (KAB26-18) - SMILES: O=[N+]([O-])C1=CC=C(C2N(C(C)=O)CCC3=CC(OC)=C(OC)C=C32)C=C1, InChI: InChI=1S/C19H20N2O5/c1-12(22)20-9-8-14-10-17(25-2)18(26-3)11-16(14)19(20)13-4-6-15(7-5-13)21(23)24/h4-7,10-11,19H,8-9H2,1-3H3, InChIKey: OIFIJKJQAGAGKY-UHFFFAOYSA-N.

Procedure
NOTE: All THF was dried over microwave activated 3 Å molecular sieves (2.0-2.5 mm) >72 h prior to use. All acetonitrile was dried over microwave 3 Å molecular sieves (2.0-2.5 mm) >24 h prior to use.[1] All glassware used was dried overnight at 115 °C.


Summary and Conclusion


References
[1] D. Bradley, G. Williams and M. Lawton, J. Org. Chem. 2010, 75, 8351. DOI: 10.1021/jo101589h Paper.
[2] H. Ishitani and S. Kobayashi, TetLett 1996, 37, 7357.
[3] S. Watanabe, Y. Kobayashi, T. Arai, H. Sasai, M. Bougauchi and M. Shibaski, TetLett 1998, 39, 7353.
[4] Rare-Earth Metal Triflates in Organic Synthesis, S. Kobayashi, M. Sugiura, H. Kitagawa and W. W.-L. Lam, Chem. Rev. 2002, 102, 2227–2302. DOI: 10.1021/cr010289i Paper.

------------------------------------------
NOTES
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]]>2012-07-27T02:34:00+01:002012-07-27T02:36:07+01:006eb3c5aa8646b56d5125734cbb059cf08http://www.ourexperiment.org/uri/29ahttps://www.ourexperiment.org/racemic_pzq/6217/PyBOX2YbOTf3_catalysed_asymmetric_acylPS_formation_of_KAB2621.htmlhttps://www.ourexperiment.org/racemic_pzq/6217/PyBOX2YbOTf3_catalysed_asymmetric_acylPS_formation_of_KAB2621.htmlhttps://www.ourexperiment.org/racemic_pzq/6217/PyBOX2YbOTf3_catalysed_asymmetric_acylPS_formation_of_KAB2621.xmlhttps://www.ourexperiment.org/racemic_pzq/6217/PyBOX2YbOTf3_catalysed_asymmetric_acylPS_formation_of_KAB2621.pnghttps://www.ourexperiment.org/racemic_pzq/6217/PyBOX2YbOTf3_catalysed_asymmetric_acylPS_formation_of_KAB2621.xml?revision=6217https://www.ourexperiment.org/racemic_pzq/6217/PyBOX2YbOTf3_catalysed_asymmetric_acylPS_formation_of_KAB2621.xml?revision=6218https://www.ourexperiment.org/racemic_pzq/6217/PyBOX2YbOTf3_catalysed_asymmetric_acylPS_formation_of_KAB2621.xml?revision=6220https://www.ourexperiment.org/racemic_pzq/6217/PyBOX2YbOTf3_catalysed_asymmetric_acylPS_formation_of_KAB2621.xml?revision=7269
62177269(PyBOX)<sub>2</sub>-Yb(OTf)<sub>3</sub> catalysed asymmetric acyl-PS formation of KAB26-21
Experiments
plus.google.com-+KatrinaBadiolaKatrina Badiola [b][u]Hazard and Risk Assessment[/b][/u] [data]4712[/data] [b][u]Previous Experiments[/b][/u] [blog]6069[/blog] [blog]6168[/blog] [b][u]Chemical Information[/u][/b] [b]2-(3,4-dimethoxyphenyl)-N-(4-nitrobenzylidene)ethanamine (MNR42-1)[/b] - SMILES: O=[N+]([O-])C1=CC=C(/C=N/CCC2=CC(OC)=C(OC)C=C2)C=C1, InChI: InChI=1S/C17H18N2O4/c1-22-16-8-5-13(11-17(16)23-2)9-10-18-12-14-3-6-15(7-4-14)19(20)21/h3-8,11-12H,9-10H2,1-2H3/b18-12-, InChIKey: LMBMXYXQVBPKHJ-PDGQHHTCSA-N. [b]1-(6,7-dimethoxy-1-(4-nitrophenyl)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone (KAB26-18) -[/b] SMILES: O=[N+]([O-])C1=CC=C(C2N(C(C)=O)CCC3=CC(OC)=C(OC)C=C32)C=C1, InChI: InChI=1S/C19H20N2O5/c1-12(22)20-9-8-14-10-17(25-2)18(26-3)11-16(14)19(20)13-4-6-15(7-5-13)21(23)24/h4-7,10-11,19H,8-9H2,1-3H3, InChIKey: OIFIJKJQAGAGKY-UHFFFAOYSA-N. [b][u]Procedure[/b][/u] [i]NOTE: All THF was dried over microwave activated 3 Å molecular sieves (2.0-2.5 mm) >72 h prior to use. All acetonitrile was dried over microwave 3 Å molecular sieves (2.0-2.5 mm) >24 h prior to use.[1] All glassware used was dried overnight at 115 °C.[/i] [b][u]Summary and Conclusion[/b][/u] [b][u]References[/b][/u] [1] D. Bradley, G. Williams and M. Lawton, [i]J. Org. Chem.[/i] [b]2010[/b], [i]75[/i], 8351. DOI: 10.1021/jo101589h [url=http://dx.doi.org/10.1021/jo101589h]Paper[/url]. [2] H. Ishitani and S. Kobayashi, [i]TetLett[/i] [b]1996[/b], [i]37[/i], 7357. [3] S. Watanabe, Y. Kobayashi, T. Arai, H. Sasai, M. Bougauchi and M. Shibaski, [i]TetLett[/i] [b]1998[/b], [i]39[/i], 7353. [4] Rare-Earth Metal Triflates in Organic Synthesis, S. Kobayashi, M. Sugiura, H. Kitagawa and W. W.-L. Lam, [i]Chem. Rev.[/i] [b]2002[/b], [i]102[/i], 2227–2302. DOI: 10.1021/cr010289i [url=http://dx.doi.org/10.1021/cr010289i]Paper[/url]. ------------------------------------------ NOTES ------------------------------------------]]>FINISH: 27/07/12




Hazard and Risk Assessment
HRA KAB26-18


Previous Experiments
Preparation of MNR42-1
Yb(OTf)3/PyBOX catalysed asymmetric acyl-PS formation of KAB26-17

Chemical Information
2-(3,4-dimethoxyphenyl)-N-(4-nitrobenzylidene)ethanamine (MNR42-1) - SMILES: O=[N+]([O-])C1=CC=C(/C=N/CCC2=CC(OC)=C(OC)C=C2)C=C1, InChI: InChI=1S/C17H18N2O4/c1-22-16-8-5-13(11-17(16)23-2)9-10-18-12-14-3-6-15(7-4-14)19(20)21/h3-8,11-12H,9-10H2,1-2H3/b18-12-, InChIKey: LMBMXYXQVBPKHJ-PDGQHHTCSA-N.
1-(6,7-dimethoxy-1-(4-nitrophenyl)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone (KAB26-18) - SMILES: O=[N+]([O-])C1=CC=C(C2N(C(C)=O)CCC3=CC(OC)=C(OC)C=C32)C=C1, InChI: InChI=1S/C19H20N2O5/c1-12(22)20-9-8-14-10-17(25-2)18(26-3)11-16(14)19(20)13-4-6-15(7-5-13)21(23)24/h4-7,10-11,19H,8-9H2,1-3H3, InChIKey: OIFIJKJQAGAGKY-UHFFFAOYSA-N.

Procedure
NOTE: All THF was dried over microwave activated 3 Å molecular sieves (2.0-2.5 mm) >72 h prior to use. All acetonitrile was dried over microwave 3 Å molecular sieves (2.0-2.5 mm) >24 h prior to use.[1] All glassware used was dried overnight at 115 °C.


Summary and Conclusion


References
[1] D. Bradley, G. Williams and M. Lawton, J. Org. Chem. 2010, 75, 8351. DOI: 10.1021/jo101589h Paper.
[2] H. Ishitani and S. Kobayashi, TetLett 1996, 37, 7357.
[3] S. Watanabe, Y. Kobayashi, T. Arai, H. Sasai, M. Bougauchi and M. Shibaski, TetLett 1998, 39, 7353.
[4] Rare-Earth Metal Triflates in Organic Synthesis, S. Kobayashi, M. Sugiura, H. Kitagawa and W. W.-L. Lam, Chem. Rev. 2002, 102, 2227–2302. DOI: 10.1021/cr010289i Paper.

------------------------------------------
NOTES
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